


when you play, play hard

by Siriusstuff



Series: Generation X++: AO3 Tag Generator Prompt Fics [4]
Category: Teen Wolf (TV)
Genre: Alternate Universe, Anal Fingering, Anal Sex, Bottom Derek Hale, Derek gets spanked, Established Relationship, M/M, Prompt Fic, Sexual Roleplay, Spanking, Top Stiles Stilinski
Language: English
Status: Completed
Published: 2015-07-11
Updated: 2015-07-11
Packaged: 2018-04-08 20:47:52
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,315
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4320132
Author URL: https://archiveofourown.org/users/Siriusstuff/pseuds/Siriusstuff
Summary: <blockquote class="userstuff">
              <p>Stiles and Derek are novices at sexual role-playing, and it shows.</p>
            </blockquote>





	when you play, play hard

**Author's Note:**

> The AO3 Tag Generator was "sexy werewolf spanking."
> 
> I've never written anything like this before, which may become blatantly obvious.
> 
> The title comes from a quote by Theodore Roosevelt.

After waving goodbye to his dad as the cruiser drove away Stiles trotted up the stairs to his bedroom.

There, clad in leather jacket, black Henley, jeans and boots, was the big bad wolf himself— _Stiles’s_ big bad wolf, Derek Hale, who stood in the midst of the room, already watching the doorway and awaiting Stiles’s appearance.

Stiles stopped at the door but was not startled. Instead he set his shoulders and leveled a look at his werewolf lover, his mouth set somewhere between lascivious leer and sexy smile.

“So…” he drawled, “creeping on my roof till my dad left, were you, big guy?”

“Was waiting in a tree first,” Derek admitted, “then jumped on your roof.”

“Waiting in a tree!” Stiles laughed.

He entered his room and started slowly circling Derek, looking him up and down. He could hear Derek breathing deeply.

“What _will_ the neighbors think,” Stiles said.

Derek, keeping mute, followed Stiles’s movement every time he crossed in front of him. Derek still had his hands in his jacket pockets.

Stiles kept circling.

“What’s it gonna take, my man, for you to come in through the front door like a respectable citizen?”

(Stiles realized he might sound like his old man with that one. But, oh well.)

Derek was scowling—but that _was_ his resting face sometimes.

Stiles stopped right in front of Derek. “Wait. I remember now,” he said. “I remember you telling me you’d appreciate _firm guidance_ in sorting out all these rules for proper social etiquette.” He resumed circling.

“’ _Firm guidance_ …’ yes,” Stiles talked on as he walked round and round. “But I, mere squishy human, know I’m up against a mighty, muscley werewolf.—Unlike _you_ —”

Again Stiles stopped in front of Derek’s face, its expression encompassing suspicion, interest—and maybe a little—worry?

“You forget you’re messin’ with a _spark_.’’ Stiles held up his hands and twiddled all his fingers. “Except I’m not just a little spark any more. I’m a great big bonfire!” He started circling again. “And I can make big bad wolfie my widdle puppy dog.”

Revolving round Derek again after a few seconds Stiles began slowly chanting.

_Stilinski has a Big Bad Wolf_

_His fur is black as coal._

_Stilinski speaks and Wolf obeys_

_For Stilinski owns his soul._

 

_Wolf broke into Stilinski’s room_

_Which was against the rules._

_For that trespass Stilinski got_

_The Wolfman by his jewels._

 

Stiles, eyes glittering, finished the incantation standing before Derek.

“That was a binding spell, Derek. You can’t move now. Unless I let you.—Can you move?”

Derek just stared at Stiles.

“You can speak,” Stiles decreed.

“No. Can’t move,” Derek said.

Stiles went to his desk and from a drawer removed a clear plastic bag with a dark powder in it. At his doorway he laid down a line of powder, then lined the sill of each window with the powder, saving for last the window Derek preferred as his entrance and exit.

Stiles put back the bag, wiped off his hands and returned to Derek.

“No running off for you now.—You can take your hands out of your pockets,” he advised. Derek did so.

“Current studies find education is most effective when it’s interactive. So, you tell me—what do you think should be the first step in teaching you how to be a gracious guest in someone’s home? My home especially.”

“I—should be—” Heavy exhale. “—punished. For entering your home uninvited,” Derek answered. There was a flush in his cheeks, visible through the shadow of his facial scruff, and he sounded a little hoarse.

“Oh. Kay. Cuttin’ right to the chase there.—Just for the record, ‘bringing the host a gift’ would have been an acceptable answer too,” Stiles said, doing his best not to snicker.

But Derek glared, and Stiles collected himself, got back on script.

“Punished.” Stiles let the word hang. He couldn’t dwell on it, but he wouldn’t shirk his role either.

“Punished,” Stiles repeated. He lowered his voice as he leaned into Derek. “Punished. How?”

Very softly Derek replied, “Spanking.” He closed his eyes.

 _That_ brought Stiles back.

“Spanking it shall be then.—Through those jeans?”

“No.”

 _Thank god_ , Stiles thought. The first time they tried that it had hurt his hands so fucking much.

“OK. So… Lose the jacket?”

Once the jacket was tossed aside Stiles ran a hand along the soft fabric of Derek’s Henley. Its softness only emphasized the hardness it covered.

Looking up he caught Derek’s eyes, so he shrugged and said, “All of it—off.”

Derek pulled his shirt over his head, off his arms.

Near the top of Stiles’s never-gonna-happen list was: _not_ getting distracted by Derek’s chest, with its perfect scatter of hair, by those pectoral muscles and those abdominals and by the fine fuzziness there which just beckoned Stiles to follow it, down, down, down—

Derek sank into a crouch to unlace a boot. Stiles would’ve helped unlace the other one but there was no way he could access it given the crouched position Derek was in.

“Why’d you wear _them_?” Stiles asked.—He dared anyone to stay on script while Derek undressed before their eyes.

So Stiles stood there while Derek’s boots and socks came off. He rubbed his hands together, over and over. Warming up his hands, he’d learned, was good spanking prep plus got him thinking about his hands’ upcoming purpose. Which helped because—

Derek stood upright once more, bare chest and barefoot. Stiles grabbed Derek’s jeans at their waist, unbuttoned and unzipped them. He tugged them open then let go, returning to his circling while Derek shoved down his pants.

Feeling suddenly very warm, Stiles removed the flannel shirt from over his tee. He saw Derek’s nostrils flare as Stiles’s scent hit him.

Back to his circle-walking, Stiles began repeating the enchantment, in a sing-song whisper.

_Stilinski has a Big Bad Wolf_

_His fur is black as coal._

_Stilinski speaks and Wolf obeys_

_For Stilinski owns his soul…_

 

In just his black boxer briefs then, Derek stood still. Stiles got close, his hand at rest on the black material concealing Derek’s butt. He whacked it lightly.

“Through these?” he asked.

Derek shook his head.

“OK. Off with ‘em.”

Naked, Derek tossed the shed briefs to where his jacket and Stiles’s shirt lay with the rest of his clothing.

“Stand up straight, you’re spelled,” Stiles reminded.

With Derek in a kind of at-attention posture, looking straight ahead, Stiles aligned himself perpendicular to Derek’s shoulder. He rubbed his nose, his face, against that shoulder, drawing in the green and woodsy notes of Derek’s odor, feeling the scent sink in like intoxication. Stiles’s left hand rode the abdominal undulations as Derek’s breaths rolled in and out. His right hand was on Derek’s back. He lowered that hand, caressing bare ass, kneading first one cheek, then the other.

Since Derek’s admission that he wanted to experience what spanking felt like Stiles had studied. He’d learned a lot and with his usual acuity. He cupped his hand, drawing back his arm, cocked for the first blow upon the chosen cheek. His hand came down and skin smacked skin. Stiles watched Derek’s face to glimpse the impact’s effect.

It had truly amazed Stiles the very first time he’d spanked him, seeing Derek both wince at the sting and then close his eyes in— _contentment_.

That very thing happened again, with a little jolt of Derek’s shoulders.

Stiles gently rubbed the spot he’d just struck, imagining his red hand print fading away faster than a ripple in a pool of water.

He lined up his hand with the other cheek and spanked that one, harder than the first. He switched up cheeks for a half dozen swats. He wanted to hear Derek make a sound; that’s how he knew the werewolf was getting what he wanted. Derek’s fists were clenched but his cantilevered cock was a good sign Stiles was delivering as desired.

This was only the warm-up. In fact, it was only a tease.

Stiles guided Derek to the bedside where he gently compelled him forward so that he leaned over, propped on his arms. The new position put Derek’s butt _right there._

“Spread your legs a little,” came the request.

Stiles was keeping to Derek’s side. The view from behind would have been _way_ too distracting, and Stiles’s hard-on, trapped in his pants, was already threatening to hijack the evening’s agenda and impose its own.

Derek’s head hung down. Whether he was patiently or impatiently waiting Stiles couldn’t tell.

Stiles closed his eyes, resting his left hand on Derek’s back, right at the bend. His other hand massaged Derek’s ass some more. His fingers tickled over the furry hole wherein lay Derek’s private entrance—not so private any more.

Derek’s moan was so soft Stiles thought he might have imagined it. So he probed deeper, let his fingers brush against the hot pucker, and that time Derek definitely moaned.

It was motivating.

Stiles started with the lightest taps, one after the other, quick-paced. The taps got harder quickly once again landing on one ass cheek then the other until full spank mode was attained.

Derek’s body jolted with each smack. Sometimes he even had to readjust his footing. Stiles was doing his best to keep count while still watching Derek react. He really wished he could see Derek’s face.

After fifteen hard swats Stiles hand was stinging so he paused. Derek was breathing hard like he’d been running.

“We’re not done,” Stiles warned. “Far from it.”

He landed a very hard spank, heard Derek “ _umph_!” Before the red print faded Stiles spanked it again. If he kept up the blows the redness lasted. It became a challenge to Stiles to keep the red there.

Before he knew it he’d delivered twenty more smacks to Derek’s ass. The wolfman glistened with sweat and once the rain of blows desisted he hung his head low between his arms.

Stiles determined to invest in a leather glove, pliant, snug-fitting. He felt sure he could spank Derek all night with that on his hand.

Stiles’s desk chair, which his dad had got him for his last birthday, was a quality one. Its arms folded up out of the way. Stiles retrieved the chair and rolled it to the midst of his room.

Derek remained where he was, still leaning over at the bedside where Stiles had left him.

Stiles seated himself and patted his thighs. Derek didn’t move.

“Derek,” Stiles announced, “stand up, turn around, look at me.”

Derek did exactly as told. His cock stuck out, curved up, outrageously hard.

Stiles patted his thighs again and watched how Derek did exactly nothing in response.

“Come over here, Derek. Stretch out.” Stiles waved a hand over his lap.

Holding up his stiff dick against his stomach and out of the way, Derek maneuvered himself till he lay across Stiles’s knees. His feet still reached the floor, his hands rested on it at the other end.

Stiles helped adjust Derek’s placement so he was—comfortable?—though the comfort would be temporary.

Derek’s body was a great weight in Stiles’s lap, though not one he couldn’t bear. The heft of it pressed down Derek’s cock so that it felt like a firebrand even through the thick material of Stiles’s jeans. Derek’s position, lying on his stomach, exposed and vulnerable, apparently hardened and heated him up all the more.

Before Stiles’s eyes lay a feast: Derek’s broad back, skin without flaw, the black triskele tattoo between his shoulder blades… Not just the sense of sight was served either: Stiles couldn’t keep his hand, his left one, from sweeping up and down the expanse of sweat-moist flesh, savoring how he could detect ribcage, the notches of the spine, the knit of muscles across Derek’s back, beneath his palm.

Under Stiles’s right hand was Derek’s ass and Stiles had not stopped rubbing over the hot spots still there, though cooling. He’d have to start spanking again soon.

Without any warning Stiles let a hard smack land right on the meatiest part of Derek’s left cheek. Derek jerked, but kept silent.

Stiles really wanted to spank some kind of sound from Derek. He couldn’t see his face now so he lacked confirmation of the impact he was having.

Lack of view reminded Stiles then how a mirror would be a great prop, across from where he sat. It still wouldn’t reveal Derek’s face but with a mirror he’d be able to see, to take it all in, how Derek looked stretched out and bent over his lap.

(Stiles added “mirror” to his shopping list, along with glove.)

The whole naked man/clothed man kink thing, his big, beautiful boyfriend, built like an athlete, slumped over, naked, ass up, Stiles’s to control—it made heat, body heat, sexual heat, bloom all over Stiles, flood into his limbs up his neck into his face. He even felt the heat tingling across his scalp.

It became a kind of energy, a fuel.

Stiles decided not to rub after each blow. He was spanking werewolf ass and until he found some spell to sensitize that skin, for all that it was supple and yielding, the lycanthrope tolerance for pain rendered it tough as rhinoceros hide.

Then three strikes to the same place, definitely not spanking manual approved technique, wrung a gasp from Derek.

“OK there, big guy?” Stiles asked. He didn’t stop spanking, though he slowed the spanks’ pace and lightened their force.

Derek answered with something that sounded like “yeah.”

“You say ‘yes’?”

”Ye-ahh,” Derek confirmed.

Now that he heard Derek’s voice Stiles was conscious of its frayed sound, the few words being blown out by heavy exhalations.

Stiles was finally beginning to feel the evening’s performance was a success!

But with that feeling he realized he was forgetting something very important: the instruction dimension to a spanking. Derek was supposed to be learning a lesson in all this ass-smacking, wasn’t he? Stiles had neglected to prepare that lesson. But winging it was one of the Stilinski fortés. Stilinski men were geniuses at winging it.

Stiles had a rhythm now, landing spanks of moderate force, switching up their points of impact. Derek, Stiles was sure, felt every one.

“Derek!” Stiles declared. “Derek?”

“Hunh?—Ye-ah?” came Derek’s distracted reply. He’d turned his head to be heard better.

“Do you know what Miss Manners says about entering someone’s home through a window?”

After no answer, “Do you, Derek?” Stiles asked pointedly, with an especially hard smack.

“No,” Derek responded, almost mournfully.

With every few syllables accented by swats, Stiles answered his own question: “The same thing Miss Manners says about arriving at a party by being shot out of a canon, Derek. _Nothing_! Nothing! Because it’s nowhere in the universe of polite behavior!”

Stiles’s right hand was _done_ , as on fire as Derek’s ass.

“Get up,” Stiles instructed, and Derek clumsily got off Stiles’s lap and upright.

“Don’t rub your butt!” stopped Derek’s move to do that very thing.

Stiles was feeling the dom role for real for the first time all night, despite also wishing he could soak his poor hand in some cold water.

“Get on the bed, on your back, Derek.”

Stiles had seen it on spank blogs and in spank porn, the “diaper-changing position.” He instructed Derek to lie on his back, parallel to the foot of the bed. Stiles lifted Derek’s legs and raised them straight up as they’d go, then told Derek take a hold of them, hands cuffing his knees.

Stiles’s head swam at the sight. Finally he could see Derek’s face too, and it was flushed, slick with sweat.

Though Stiles knew it was rapidly restoring itself, Derek’s ass was still rosy pink, plainly in view with his legs up in the air.

Stiles adjusted his rigid dick in his pants and took a seat on the bed side, on Derek’s right, but twisted around to look at his ass-smacked boyfriend.

“Derek?” he asked.

Derek just looked him in the eyes, panting still.

“Do you wish your spanking was over?—Answer me honestly,” Stiles ordered, as the mage in command.

Derek nodded a few slow nods, but said nothing.

Stiles just smirked. “There’s a saying among spankers, addressed to spankees. It goes: ‘A proper spanking doesn’t really start until you wish it was over.’—Know what that means?”

Derek closed his eyes and nodded again.

“Alrighty then,” Stiles concluded.

Considering his right hand probably hurt more than Derek’s butt—and would definitely hurt for longer—Stiles used to his left hand for the spank-finale. He stayed seated. But in the legs-up position Derek’s butt muscles were taut and any slap would sting like bloody hell now.

“Count ‘em off, big guy,” Stiles insisted, and let the first spank fly.

“One,” Derek said, followed by a huff.

Stiles free-styled the final set. His seated position was awkward enough to blunt the force of the spanks being pitched. But at “Six,” Derek groaned, tilted back his head. So Stiles decided four more would be enough, though he’d focus for these last four, two on each cheek, maybe the hardest his left arm could hit.

Derek gulped and whined from the count of seven through ten, and at “Ten,” Stiles stopped.

He stood and held up Derek’s legs by the ankles.

“Let go,” Stiles ordered.

Derek dropped his arms as if they’d been holding up a great weight.

Stiles parted Derek’s legs some, wish-bone like, to find the werewolf already looking at him.

They stared at each another silently for a few beats. Well, silently apart from Derek’s snort-like exhales.

“You want my dick?” Stiles asked him.

Derek silently nodded, breaths heaving.

“ _Good_ —‘cause I _really_ wanna give it to you.”

Stiles lowered Derek’s legs, dashed to his little bedside table, where he kept his lube. First he got out of his pants and underwear, leaving them on the floor, topped by his t-shirt. He decided to lube and finger Derek’s hole open first, because if he touched his dick too much he might just come standing right there.

“Hey, what’s goin’ on, big bad?” he asked when he saw Derek’s head still rolled back, could hear his breaths still deep, still tense.

“You’ll feel better soon,” Stiles assured, after Derek didn’t answer.

Tickling two thickly coated fingers against Derek’s asshole, Stiles was sure the cool lube would feel relieving. He gently twisted his long middle finger inside. The tightness, the heat, just past Derek’s anal ring always felt kind of astonishing to Stiles. He sank the finger in deep, swirling it around, sure that somewhere in there was Derek’s prostate. When he saw, heard, Derek’s breath change, his head start to loll from side to side— _yeah_ , he’d hit the spot.

“Feels good, hunh,” Stiles said, his voice low.

When Derek still didn’t respond, Stiles coaxed, “C’mon, Derek, talk to me.”

“Yes,” Derek finally answered, softly but sincerely. “Feels—good.”

“Feels _so_ good,” Stiles repeated, adding a second finger, wriggling them together inside, pulling them partly out and scissoring them, rotating them around spread apart, stretching open Derek’s entrance.

Derek moaned, open mouthed.

With both fingers thrust deep, still scissored and twisting back and forth, their every pass over Derek’s sweet spot caused another moan. Derek had reached for his hard-on but Stiles’s “Hands off!” had arrested that intention.

“Not till I say you can!”

They were going to play this game to its end.

Stiles wasn’t sure how much longer it could go on anyway.

Stiles fingered more lube inside Derek, then slicked up his own dick, still touching it only gingerly, he felt so close to orgasm.

Since Derek was watching his every move Stiles didn’t need to tell him he was _going in_.

With Derek’s calves resting on Stiles’s shoulders he pushed inward, in one smooth glide. He felt the residual heat of Derek’s spanked ass pressed against his slightly cooler skin. The clasp of intensely hot tissue round his dick made Stiles throw his head back and almost shout, it felt _so good_.

When he looked again, Derek was smiling, faintly, but still his first smile of the whole evening.

“You feel… so good, Derek,” Stiles crooned.

“You too,” Derek murmured.

Stiles had learned if he counted his fuck-strokes sometimes that prolonged the fucking’s duration—especially when he felt as close to blowing his load as he did then.

Also, if he talked, which was rarely a problem for Stiles, it had the same effect.

“OK,” he half spoke, half gasped. “I’ve got another spell, Derek. Listen:”

_Derek be nimble,_

_Derek be quick,_

_Derek may jerk off_

_His great big dick!_

Derek closed his eyes, as if he were stifling a laugh, but then immediately started stripping up and down his stiff cock. The look on his face quickly transitioned from quashed giggle to pleasure-on-its-way.

A hard sigh escaped him.

Stiles pounded and counted. The exact location of Derek’s internal joy button was still uncertain to Stiles, but he sought it valiantly, canting his hips at various angles, flexing his dick so it rode up against the tissue of Derek’s rectum.

The vaulting speed and intensity of Derek’s jerking off showed Stiles he _had_ to be hitting his target and hitting it hard, because he felt a kind of counter motion to his non-stop thrusting, as if Derek’s body were squeezing around Stiles’s buried cock. From the corner of his eye he saw Derek’s toes start to curl.

Derek’s head was pitching back, his eyelids fluttering, his mouth hanging open. Stiles’s own furious breaths and “ _Oh fucks_ ” accompanied Derek’s moans coming closer and closer together.

Through squinting eyes Stiles saw Derek’s dick shoot spurt after spurt as he climaxed. At the same time Stiles sensed what felt like soft convulsions around his own dick and he climaxed too.

They had shared simultaneous orgasms, a celebrated achievement for couples, but Stiles would only realize that later on. At that moment he was absorbed in rubbing his face against one of Derek’s calves and kissing whatever part of his lover was closest to his lips.

When he was able to open his eyes, again Derek was staring right at him.

“You OK?” Stiles asked. His heart was wide open, his few words full of love and caring.

“I’m fine, Stiles,” Derek answered.

“You _are_ fine, baby. The _finest_.”

Derek made a face. Stiles whimpered in response, let Derek’s legs slide down his sides. He clambered awkwardly onto the supine werewolf, whose arms came up and around him. While still in their awkward positions, they kissed.

It was the first time they’d kissed all evening.

“How’s your butt feel?” Stiles asked, his mouth so close to Derek’s face his lips touched skin when he spoke.

“My butt feels spanked,” was Derek’s reply.

Stiles pulled back his head. “That’s what you wanted, _right_?”

Derek only looked at Stiles, smiling mysteriously.

“ _Right, Derek?_ ”

The smile turned to grin.

“ _You asshole!_ ”

“Come on, get up. Let’s clean up,” Derek suggested.

Stiles didn’t move. “Thought you liked spunk all over you.”

“I like yours more.” Derek levered Stiles off, got to his feet.

Stiles lay where he’d rolled. He groaned. “OK. Gimme a little while. I’ll spunk all over you, wherever you want.”

Then, “Stiles,” Derek announced from the doorway. “The line.”

Stiles was uncomprehending for a moment, lifting his head and looking at Derek.

“What?”

“Break the line, Stiles.”

Stiles sat up with a shrug already in place. “I _know_ you can smell that’s it’s cocoa powder…”

“Just—break it.”

Amazed at how seriously Derek took the rules of their game, Stiles stomped to where Derek stood. He fanned a hand over the line of powder on the floor across the doorway so Derek could step past it, stalk down the hall to the bathroom. With a hand vacuum Stiles sucked up the remaining powder as well as all of it from all the window sills. Didn’t want to be attracting ants indoors.

He joined Derek in the bathroom, where he’d already wiped himself off and was ready with a warm wet cloth to wipe down Stiles.

Cleaned up, they kissed some more.

“Let’s get back to bed. I need to get my cuddle on,” Stiles said.

Before lying down Stiles asked to have a look at Derek’s backside. He wondered if he was imagining he could still see some pinkness, pinkness not usually there beneath the fuzziness of Derek’s splendid ass.

“You never answered me. Are you gonna keep bein’ a little shit and _not_ tell me if I did OK.—Did I feed your need?”

Facing him Derek drew Stiles close, dragged his scruffy face along Stiles’s neck and throat, more cat-like than any other type of beast.

After a few silent minutes of that Stiles had a kind of epiphany.

“OK,” he said quietly, finally relaxed and assured. “I get it.”

Derek’s pouty smile and the shy cast of his eyes said everything.

“Come on. Let’s lie down. I want to spoon,” Stiles whispered.

Derek lay down first, so Stiles could spoon around him. Stiles’s nuzzling and kissing the back of his neck soothed Derek thoroughly, still he asked, “Isn’t it kind of early for bed?”

“Shhh. Paddling your ass is a workout. Stiles needs a little nap before we do anything else.”

“Gonna spell me to sleep?” Derek wondered.

“How ‘bout a lullaby?”

The little quake Stiles felt was Derek’s laugh. In response he just started singing.

_Soft werewolf,_

_Warm werewolf,_

_Creeper on my roof._

_Happy werewolf,_

_Sleepy werewolf,_

_Woof, woof, woof._

 

“That’s not a lullaby,” Derek whispered. Stiles could hear his smile.

“Shh,” Stiles whispered back, anchoring himself with an arm round Derek’s chest and pulling himself flush against him, so his mouth was right at Derek’s ear. “It is if you’d just take a nap.”

**Author's Note:**

> In case anyone doesn't realize, both of Stiles's "spells" are derived from Mother Goose rhymes, "Mary had a little lamb," and "Jack be nimble." The lullaby at the end is my take on the werewolf version of Soft Kitty, from The Big Bang Theory. It's a revision of what AsagiStilinski uses in the fic Happy Werewolf, Sleepy Werewolf, which I tweaked so the whole thing rhymes. (P.S. AsagiStilinski liked it!)


End file.
